Sulfamide

Sulfamide^[1]

Names
IUPAC name Sulfuric diamide
Other names Sulphamide Sulfuryl amide
Identifiers
CAS Number	7803-58-9
ChEBI	CHEBI:29368
ChEMBL	ChEMBL355001
ChemSpider	74243
Jmol interactive 3D	Image
PubChem	82267
InChI InChI=1S/H4N2O2S/c1-5(2,3)4/h(H4,1,2,3,4) Key: NVBFHJWHLNUMCV-UHFFFAOYSA-N InChI=1/H4N2O2S/c1-5(2,3)4/h(H4,1,2,3,4) Key: NVBFHJWHLNUMCV-UHFFFAOYAV
SMILES O=S(=O)(N)N
Properties
Chemical formula	H4N2O2S
Molar mass	96.11 g/mol
Appearance	White orthorhombic plates
Melting point	93 °C (199 °F; 366 K)
Boiling point	250 °C (482 °F; 523 K) (decomposes)
Solubility in water	Freely soluble
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Sulfamide (IUPAC name: sulfuric diamide) is a chemical compound with the molecular structure H₂NSO₂NH₂. Sulfamide is produced by the reaction of sulfuryl chloride with ammonia. Sulfamide was first prepared in 1838 by the French chemist Henri Victor Regnault.^[2]

Sulfamide functional group

In organic chemistry, the term sulfamide may also refer to the functional group which consists of at least one organic group attached to a nitrogen atom of sulfamide.

Symmetric sulfamides can be prepared directly from amines and sulfur dioxide gas:^[3]

In this example, the reactants are aniline, triethylamine, and iodine. Sulfur dioxide is believed to be activated through a series of intermediates: Et₃N-I⁺-I⁻, Et₃N-I⁺-I₃⁻ and Et₃N⁺-SO₂⁻.

The sulfamide functional group is an increasingly common structural feature used in medicinal chemistry.^[4]

See also

• Sulfamic acid
• Sulfonamide (chemistry)

References

1. Merck Index, 11th Edition, 8894.
2. Regnault, Victor (1838) "Sur l'acide chlorosulfurique et la sulfamide" (On sulfuryl chloride and sulfamide), Annales de chimie et de physique, series 2, 69 : 170-184; see especially "Action de gaz ammoniac sec sur la liqueur chlorosulfurique" (Action of dry ammonia gas on liquid sulfuryl chloride), pages 176-180.
3. Leontiev, A. V.; Dias, H. V. R.; Rudkevich, D. M. (2006). "Sulfamides and sulfamide polymers directly from sulfur dioxide". Chemical Communications 2006 (27): 2887–2889. doi:10.1039/b605063h.
4. Reitz‌, A. B.; Smith‌, G. R.; Parker‌, M. H. (2009). "The Role of Sulfamide Derivatives in Medicinal Chemistry: A Patent Review (2006 – 2008)". Expert Opinion on Therapeutic Patents 19 (10): 1449–1453. doi:10.1517/13543770903185920. PMID 19650745.